143685-68-1Relevant articles and documents
N-(6-Methyl-2-pyridyl)acrylamide: a case of amide hydrolysis without the assistance of acid or base in the synthesis of water-driven H-bonded polymeric chains
Ghosh, Kumaresh,Sen, Tanushree,Fr?hlich, Roland
, p. 6308 - 6311 (2007)
Amide hydrolysis of N-(6-methyl-2-pyridyl)acrylamide without the assistance of either acid or base produces the aminopyridinium carboxylate salt at low or room temperature. The carboxylate ion and the free amine functionalities are cooperatively involved in hydrogen bonding with lattice water to form a new hydrogen-bonded polymeric chain.
Synthesis of 4-Trifluoromethylated 1,3-Butadienes via Palladium Catalyzed Heck Reaction
Li, Yang,Hao, Meng,Chang, Yu-Chen,Liu, Yuan,Wang, Wen-Fei,Sun, Ning,Zhu, Wen-Qing,Gao, Ziwei
supporting information, p. 2962 - 2966 (2021/08/23)
1,3-Butadiene plays a key role in modern synthetic chemistry and biochemistry because it is a key intermediate in the synthesis of many drugs. A new and effective method for the synthesis of 4-trifluoromethylated 1,3-butadiene through the fluorinated Heck reaction catalyzed by Pd(0) is described. Without additives, 1-chloro-3,3,3-trifluoropropene (an inexpensive CF3 structural unit that is harmless to ozone) reacts with enamide to synthesize 4-trifluoromethylated 1,3-butadienes with good yield, high regioselectivity and chemical selectivity, and strong tolerance of substrate functional groups such as alkynes, aldehyde, and ester groups.
Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes
Gouverneur, Véronique,Hell, Sandrine M.,Laudadio, Gabriele,Meyer, Claudio F.,Misale, Antonio,No?l, Timothy,Trabanco, Andrés A.,Willis, Michael C.
supporting information, p. 720 - 725 (2020/02/20)
Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.
Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation
Eriksson, Jonas,Aberg, Ola,Langstroem, Bengt
, p. 455 - 461 (2008/02/03)
Two methods are presented for the synthesis of acrylamides labelled with 11C (β+, t1/2 = 20.4 min) and 13C in the carbonyl position. In the first method, [1- 11C]acrylic acid is synthesised from [11C]carbon monoxide by palladium-mediated hydroxycarbonylation of acetylene. The labelled carboxylic acid is converted into the acyl chloride and subsequently treated with amine to yield N-benzyl[carbonyl-11C]acrylamide. The second method utilizes [11C]carbon monoxide in a palladium-mediated carbonylative cross-coupling of vinyl halides and amines. A higher radiochemical yield is achieved with the latter method and the amount of amine needed is decreased to 1/20. The 11C-labelled acrylamides were isolated in up to 81 % decay-corrected radiochemical yield. Starting from 10 ± 0.5 GBq of [ 11C]carbon monoxide, N-benzyl[carbonyl-11C]acrylamide was obtained in 4 min with a specific radioactivity of 330 ± 4 GBq μmol-1. Co-labelling with 11C and 13C enabled confirmation of the labelled position by 13C NMR spectroscopy. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
